Dibromomethane → HCID 71110700, compound

HRID 576405Notes

Reaction equation

HRID 576405 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[C:5]([Cl:10])=[C:6]([OH:9])[C:7]=1[OH:8].Br[CH2:22]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[C:7]2[O:8][CH2:22][O:9][C:6]=2[C:5]([Cl:10])=[C:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:19][CH2:20]3)=[CH:14][CH:13]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 10796Cesium carbonateHCID 86714085HCID 86714085, compound

Product 1

HCID 71110700HCID 71110700, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of phenol 192 (1.75 g, 4.95 mmol) in DMF (25 mL) were added dibromomethane (0.42 mL, 5.94 mmol) and Cs2CO3 (5.7 g, 17.3 mmol) at r.t. The mixture was stirred at 90° C. for 12 hours. The mixture was cooled to r.t. and filtered off to remove inorganic salts. The filtrate was extracted with EtOAc/aq. 50% NaCl solution (100 mL/500 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 193 (1.17 g, 65%).

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. filtrationfiltered off
  3. customto remove inorganic salts
  4. extractionThe filtrate was extracted with EtOAc/aq
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0dc7f60124cd4b85b7761f24749efe4b
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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